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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o881.
Published online 2010 March 20. doi:  10.1107/S1600536810009694
PMCID: PMC2983847

N-(2,4-Dimethyl­phen­yl)succinimide

Abstract

In the title compound, C12H13NO2, the dihedral angle between the benzene ring and the imide segment is 85.7 (1)°. In the crystal, the mol­ecules are packed into zigzag chains parallel to the a axis.

Related literature

For our study of the effect of ring and side-chain substitutions on the structures of biologically significant compounds, see: Gowda et al. (2007 [triangle]); Saraswathi et al. (2010a [triangle],b [triangle]).

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Object name is e-66-0o881-scheme1.jpg

Experimental

Crystal data

  • C12H13NO2
  • M r = 203.23
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o881-efi1.jpg
  • a = 7.1461 (7) Å
  • b = 11.182 (2) Å
  • c = 13.676 (2) Å
  • V = 1092.8 (3) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.68 mm−1
  • T = 299 K
  • 0.50 × 0.25 × 0.25 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • 2947 measured reflections
  • 1152 independent reflections
  • 987 reflections with I > 2σ(I)
  • R int = 0.065
  • 3 standard reflections every 120 min intensity decay: 1.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.113
  • S = 1.06
  • 1152 reflections
  • 157 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 [triangle]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009694/vm2021sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009694/vm2021Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

supplementary crystallographic information

Comment

As a part of studying the effect of ring and side chain substitutions on the structures of biologically significant compounds (Gowda et al., 2007; Saraswathi et al., 2010a,b), the crystal structure of N,N-(2,4-dimethylphenyl)succinimide has been determined (Fig. 1). The dihedral angle between the benzene ring and the imide segment in the molecule is 85.7 (1)°.

The torsional angles of the groups, C2 - C1 - N1 - C7, C6 - C1 - N1 - C7, C2 - C1 - N1 - C10 and C6 - C1 - N1 - C10 in the molecule are -97.8 (3)°, 80.0 (3)°, 88.9 (3)° and -93.4 (3)°, respectively, while the torsional angles of the groups, O1 - C7 - N1 - C1, C8 - C7 - N1 - C1, O2 - C10 - N1 - C1 and C9 - C10 - N1 - C1 are 3.2 (4)°, -178.6 (2)°, -7.2 (4)° and 173.0 (2)°, respectively.

The packing of molecules into zigzag chains is shown in Fig.2.

Experimental

The solution of succinic anhydride (0.025 mole) in toluene (25 ml) was treated dropwise with the solution of 2,4-dimethylaniline (0.025 mole) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for one h and set aside for an additional hour at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 2,4-dimethylaniline. The resultant solid N-(2,4-dimethylphenyl)succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. It was recrystallized to constant melting point from ethanol.

N-(2,4-Dimethylphenyl)succinamic acid was heated for 2 h and then allowed to cool slowly to room temperature to get the compound, N-(2,4-dimethylphenyl)succinimide. The purity of the compound was checked and characterized by its infrared spectra.

The rod like colourless single crystals of the compound used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.

Refinement

The H atoms of the CH3 groups were positioned with idealized geometry using a riding model with C—H = 0.96 Å. The other H atoms were located in a difference map and their position refined to C—H = 0.91 (3)–1.06 (3) Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

In the absence of significant anomalous dispersion effects, Friedel pairs were merged and the Δf"term set to zero.

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
Molecular packing of the title compound.

Crystal data

C12H13NO2F(000) = 432
Mr = 203.23Dx = 1.235 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 7.1461 (7) Åθ = 5.1–23.4°
b = 11.182 (2) ŵ = 0.68 mm1
c = 13.676 (2) ÅT = 299 K
V = 1092.8 (3) Å3Rod, colourless
Z = 40.50 × 0.25 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.065
Radiation source: fine-focus sealed tubeθmax = 66.9°, θmin = 5.1°
graphiteh = −3→8
ω/2θ scansk = −13→13
2947 measured reflectionsl = 0→16
1152 independent reflections3 standard reflections every 120 min
987 reflections with I > 2σ(I) intensity decay: 1.0%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0693P)2 + 0.082P] where P = (Fo2 + 2Fc2)/3
1152 reflections(Δ/σ)max = 0.011
157 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = −0.17 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C1−0.0480 (4)0.0411 (2)0.04393 (17)0.0377 (6)
C2−0.2151 (4)−0.0128 (2)0.07236 (18)0.0410 (6)
C3−0.2763 (4)−0.1082 (2)0.0153 (2)0.0461 (6)
H3−0.400 (5)−0.144 (3)0.034 (2)0.055*
C4−0.1827 (4)−0.1484 (2)−0.06581 (18)0.0469 (6)
C5−0.0181 (4)−0.0909 (3)−0.0921 (2)0.0488 (7)
H50.042 (5)−0.111 (3)−0.153 (2)0.059*
C60.0488 (4)0.0035 (3)−0.0372 (2)0.0462 (7)
H60.184 (5)0.035 (3)−0.049 (2)0.055*
C7−0.0064 (4)0.2593 (2)0.06994 (18)0.0429 (6)
C80.0891 (5)0.3392 (2)0.1425 (2)0.0483 (7)
H8A0.164 (5)0.390 (3)0.107 (2)0.058*
H8B−0.013 (5)0.391 (3)0.1798 (19)0.058*
C90.1992 (5)0.2553 (3)0.2077 (2)0.0478 (7)
H9A0.182 (5)0.264 (3)0.273 (3)0.057*
H9B0.325 (5)0.267 (3)0.193 (2)0.057*
C100.1393 (4)0.1310 (2)0.17959 (17)0.0427 (6)
C11−0.3240 (5)0.0311 (3)0.1583 (2)0.0581 (8)
H11A−0.34910.11500.15070.070*
H11B−0.25290.01850.21690.070*
H11C−0.4400−0.01180.16250.070*
C12−0.2569 (6)−0.2502 (3)−0.1256 (2)0.0683 (10)
H12A−0.2704−0.3197−0.08490.082*
H12B−0.1714−0.2674−0.17790.082*
H12C−0.3765−0.2288−0.15230.082*
N10.0217 (3)0.14153 (17)0.09856 (13)0.0376 (5)
O1−0.0975 (3)0.28747 (18)−0.00034 (16)0.0666 (7)
O20.1797 (4)0.03828 (17)0.21710 (15)0.0634 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0370 (13)0.0333 (12)0.0428 (12)−0.0018 (10)−0.0027 (11)0.0014 (10)
C20.0362 (13)0.0422 (12)0.0447 (12)−0.0015 (11)0.0014 (12)0.0064 (10)
C30.0418 (14)0.0410 (13)0.0554 (14)−0.0095 (12)−0.0025 (13)0.0064 (11)
C40.0557 (16)0.0388 (12)0.0462 (13)−0.0038 (13)−0.0092 (13)0.0017 (11)
C50.0505 (15)0.0511 (15)0.0448 (13)0.0000 (13)0.0040 (14)−0.0067 (12)
C60.0380 (14)0.0486 (15)0.0521 (14)−0.0044 (12)0.0055 (13)−0.0029 (11)
C70.0385 (13)0.0368 (12)0.0534 (13)0.0039 (11)−0.0018 (13)−0.0007 (11)
C80.0501 (16)0.0375 (13)0.0571 (15)−0.0026 (13)−0.0003 (15)−0.0054 (12)
C90.0444 (15)0.0526 (15)0.0463 (14)−0.0084 (14)−0.0032 (14)−0.0062 (12)
C100.0390 (13)0.0472 (14)0.0419 (12)−0.0021 (12)−0.0006 (11)−0.0001 (11)
C110.0522 (17)0.0627 (17)0.0595 (16)−0.0011 (16)0.0141 (15)−0.0013 (14)
C120.083 (3)0.0562 (17)0.0657 (17)−0.0156 (18)−0.0154 (19)−0.0090 (15)
N10.0353 (11)0.0353 (10)0.0422 (10)−0.0008 (9)−0.0031 (9)−0.0015 (8)
O10.0745 (15)0.0501 (12)0.0754 (12)0.0086 (11)−0.0306 (13)0.0057 (11)
O20.0710 (15)0.0525 (12)0.0665 (12)−0.0038 (11)−0.0214 (12)0.0138 (10)

Geometric parameters (Å, °)

C1—C61.373 (4)C8—C91.514 (4)
C1—C21.393 (4)C8—H8A0.92 (3)
C1—N11.438 (3)C8—H8B1.06 (3)
C2—C31.392 (4)C9—C101.505 (4)
C2—C111.493 (4)C9—H9A0.91 (3)
C3—C41.372 (4)C9—H9B0.93 (4)
C3—H31.00 (3)C10—O21.192 (3)
C4—C51.388 (4)C10—N11.396 (3)
C4—C121.498 (4)C11—H11A0.9600
C5—C61.381 (4)C11—H11B0.9600
C5—H50.97 (3)C11—H11C0.9600
C6—H61.04 (3)C12—H12A0.9600
C7—O11.203 (3)C12—H12B0.9600
C7—N11.388 (3)C12—H12C0.9600
C7—C81.499 (4)
C6—C1—C2121.6 (2)H8A—C8—H8B108 (3)
C6—C1—N1119.0 (2)C10—C9—C8105.9 (2)
C2—C1—N1119.3 (2)C10—C9—H9A108 (2)
C1—C2—C3116.4 (2)C8—C9—H9A116 (2)
C1—C2—C11121.6 (2)C10—C9—H9B110 (2)
C3—C2—C11122.0 (2)C8—C9—H9B106.8 (19)
C4—C3—C2123.5 (3)H9A—C9—H9B109 (3)
C4—C3—H3120.1 (17)O2—C10—N1124.1 (2)
C2—C3—H3116.3 (17)O2—C10—C9128.7 (2)
C3—C4—C5118.1 (2)N1—C10—C9107.2 (2)
C3—C4—C12121.2 (3)C2—C11—H11A109.5
C5—C4—C12120.7 (3)C2—C11—H11B109.5
C6—C5—C4120.4 (3)H11A—C11—H11B109.5
C6—C5—H5120 (2)C2—C11—H11C109.5
C4—C5—H5120 (2)H11A—C11—H11C109.5
C1—C6—C5120.0 (3)H11B—C11—H11C109.5
C1—C6—H6119.3 (16)C4—C12—H12A109.5
C5—C6—H6119.7 (16)C4—C12—H12B109.5
O1—C7—N1123.5 (2)H12A—C12—H12B109.5
O1—C7—C8128.3 (2)C4—C12—H12C109.5
N1—C7—C8108.2 (2)H12A—C12—H12C109.5
C7—C8—C9104.9 (2)H12B—C12—H12C109.5
C7—C8—H8A106.3 (19)C7—N1—C10113.0 (2)
C9—C8—H8A113 (2)C7—N1—C1122.9 (2)
C7—C8—H8B109.2 (18)C10—N1—C1123.7 (2)
C9—C8—H8B114.2 (15)
C6—C1—C2—C31.2 (4)C7—C8—C9—C10−8.4 (3)
N1—C1—C2—C3178.9 (2)C8—C9—C10—O2−173.7 (3)
C6—C1—C2—C11−177.6 (2)C8—C9—C10—N16.0 (3)
N1—C1—C2—C110.0 (4)O1—C7—N1—C10177.2 (3)
C1—C2—C3—C4−0.9 (4)C8—C7—N1—C10−4.6 (3)
C11—C2—C3—C4178.0 (3)O1—C7—N1—C13.2 (4)
C2—C3—C4—C50.1 (4)C8—C7—N1—C1−178.6 (2)
C2—C3—C4—C12−178.9 (3)O2—C10—N1—C7178.8 (3)
C3—C4—C5—C60.5 (4)C9—C10—N1—C7−0.9 (3)
C12—C4—C5—C6179.5 (3)O2—C10—N1—C1−7.2 (4)
C2—C1—C6—C5−0.7 (4)C9—C10—N1—C1173.0 (2)
N1—C1—C6—C5−178.4 (3)C6—C1—N1—C780.0 (3)
C4—C5—C6—C1−0.2 (4)C2—C1—N1—C7−97.8 (3)
O1—C7—C8—C9−173.9 (3)C6—C1—N1—C10−93.4 (3)
N1—C7—C8—C98.1 (3)C2—C1—N1—C1088.9 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2021).

References

  • Enraf–Nonius (1996). CAD-4-PC Enraf–Nonius, Delft, The Netherlands.
  • Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91–100.
  • Saraswathi, B. S., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o325. [PMC free article] [PubMed]
  • Saraswathi, B. S., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o390. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Stoe & Cie (1987). REDU4 Stoe & Cie GmbH, Darmstadt, Germany.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography